Method for synthesizing n-acetylsulfanilyl chloride by using sulfur trioxide as sulfonating agent

A technology of acetaminobenzenesulfonyl chloride and sulfur trioxide, applied in the preparation of sulfonic acid, organic chemistry, etc., can solve the problems of additive influence, high processing cost, and waste acid, so as to ensure quality, protect the environment, and save processing cost Effect

Active Publication Date: 2017-06-20
吴赣药业(苏州)有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Foreign production mainly adopts cryogenic drying technology equipment and spray granulation drying to make finished products, but additives have an impact on the reaction
The development trend is that the use of cryogenic drying is beneficial to the stability of the obtained product, but the investment is relatively large
In addition, the current syn

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] The present embodiment provides a method for the synthesis of acetaminobenzenesulfonyl chloride with sulfur trioxide as a sulfonating agent, which comprises the following steps:

[0016] (a) Add 13.5kg of acetanilide and 30kg of glacial acetic acid successively in the reactor, stir and heat up to 40°C;

[0017] (b) Feed sulfur trioxide gas into the reaction kettle (the flow rate of ventilation is 2.5L / min), and react at 40°C for 15 hours; when approaching the end of the reaction, sample and analyze every 15min (analyze using liquid chromatograph HPLC) , until the complete conversion of acetanilide, stop feeding sulfur trioxide gas;

[0018] (c) making the temperature in the reactor rise to 65°C, and reclaiming glacial acetic acid under reduced pressure;

[0019] (d) Control the temperature in the reactor to 60°C, add 12 kg of thionyl chloride dropwise and react for 4 hours (the tail gas is recovered with lye, such as 1mol / L sodium carbonate solution), and recover unrea...

Embodiment 2

[0021] The present embodiment provides a method for the synthesis of acetaminobenzenesulfonyl chloride with sulfur trioxide as a sulfonating agent, which comprises the following steps:

[0022] (a) Add 13.5kg of acetanilide and 60kg of glacial acetic acid successively in the reactor, and stir and heat up to 70°C;

[0023] (b) Feed sulfur trioxide gas into the reactor (the flow rate of ventilation is 13.0L / min), and react at 70°C for 3 hours; when approaching the end of the reaction, take samples for analysis every 5 minutes (analyze using liquid chromatograph HPLC) , until the complete conversion of acetanilide, stop feeding sulfur trioxide gas;

[0024] (c) making the temperature in the reactor rise to 80°C, and reclaiming glacial acetic acid under reduced pressure;

[0025] (d) Control the temperature in the reactor to 90°C, add 15 kg of thionyl chloride dropwise and react for 2 hours (the tail gas is recovered with lye, such as 1mol / L sodium carbonate solution), and recove...

Embodiment 3

[0027] The present embodiment provides a method for the synthesis of acetaminobenzenesulfonyl chloride with sulfur trioxide as a sulfonating agent, which comprises the following steps:

[0028] (a) Add 13.5kg of acetanilide and 45kg of glacial acetic acid successively in the reactor, stir and heat up to 50°C;

[0029] (b) Feed sulfur trioxide gas into the reaction kettle (the flow rate of ventilation is 8.0L / min), and react at 50°C for 5 hours; when approaching the end of the reaction, sample and analyze every 10min (analyze using liquid chromatograph HPLC) , until the complete conversion of acetanilide, stop feeding sulfur trioxide gas;

[0030] (c) making the temperature in the reactor rise to 70°C, and reclaiming glacial acetic acid under reduced pressure;

[0031] (d) Control the temperature in the reactor to 80°C, add 13 kg of thionyl chloride dropwise and react for 3 hours (the tail gas is recovered with lye, such as 1mol / L sodium carbonate solution), and recover unreac...

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PUM

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Abstract

The invention relates to a method for synthesizing n-acetylsulfanilyl chloride by using sulfur trioxide as a sulfonating agent. The method comprises the following steps: (a) sequentially adding acetanilide and glacial acetic acid into a reaction kettle, stirring and warming to 40 to 70 DEG C; (b) inflating sulfur trioxide gas into the reaction kettle, reacting for 3 to 15 hours at the temperature of 40 to 70 DEG C to enable acetanilide to be completely converted and stopping inflating the sulfur trioxide gas; (c) warming temperature in the reaction kettle to 65 to 80 DEG C and decompressing to recycle the glacial acetic acid; (d) controlling temperature in the reaction kettle as 60 to 90 DEG C, dropwise adding thionyl chloride to react for 2 to 4 hours, decompressing to recycle unreacted thionyl chloride and cooling. Therefore, quality of n-acetylsulfanilyl chloride is guaranteed, waste water and waste acid are prevented from being generated, processing cost is saved, and environmental friendliness is facilitated.

Description

technical field [0001] The invention relates to the field of synthesis of chemical intermediates, in particular to a method for synthesizing p-acetamidobenzenesulfonyl chloride by using sulfur trioxide as a sulfonating agent. Background technique [0002] Acetaminobenzenesulfonyl chloride is a pharmaceutical intermediate and the main raw material for the preparation of sulfamethoxazole and sulfathiazole and other sulfonamide drugs. At present, the domestic use is mainly for self-use, and the wet product is prepared and used immediately, otherwise it will happen. Decomposition, deterioration, and the period to achieve stable quality is only three days at most. As a real commodity, it is still blank in the market. Overseas production mainly adopts cryogenic drying technology equipment and spray granulation drying to make finished products, but additives have an impact on the reaction. The development trend is that the use of cryogenic drying is beneficial to the stability of ...

Claims

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Application Information

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IPC IPC(8): C07C303/02C07C309/88
CPCC07C303/02C07C303/06C07C309/88C07C309/51
Inventor 计建明钱炜雯朱凤林
Owner 吴赣药业(苏州)有限公司
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